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The road to starting up: A series of terrible decisions
by Katrina Brickner
"I wasn't 'poor', I was 'po'. I couldn't afford the 'o-r'." - Big L 
Luke, Alex, and I are very close-knit co-founders. Like really creepy close. Alex and I are married, and Luke is one of our best friends. We all really like each other, and genuinely enjoy each other's company. And that's a really good thing, because if we didn't, I'm convinced we never would have made it through the last 3 1/2 years. I'd like to take you through our experience of beginning two separate startups in the hope that I can prevent even one person from making the same mistakes we've made. So get ready; this won't be pretty.
Economy's in the tank, let's start a company 
The story begins in March, 2009, in sunny Miami, FL. Alex and Luke were working at an ad agency that crumbled under the weight of the recession (amongst other, more scandalous, issues), and I was looking for a job in technology. I was having trouble finding a job due to my inexperience in the field (my Master's degree in Psychology and year of case management weren't cutting it). Alex was having trouble due to his inability to assimilate into a corporate environment. And Luke...well, Luke just wanted to make something cool. 
We decided over High Life beers one night that we could totally  run our own company. How hard could it be, anyway? All we had to do was take our collective skill set, experience from working with old bosses at other companies, and just do everything way better. 
Two days later we were were all unemployed - excuse me, self employed - and on our way. 
We racked our brains to determine whose online presence could most benefit from a focused design and development team. The 2008 election had just wrapped up, Obama had shown just what could be done with a coherent online strategy, Ron Paul had raised a ton of money directly from the web, and no matter how bad the economy gets, politicians always seem to have cash in the bank. On paper, it was a great idea. Recession-proof clients, lots of reusable components, and potentially lucrative transaction fees from the fundraising platform. The three of us, and our two other co-founders, were about to make a ton of money, right?
Wrong. 
In our excitement, we overlooked a few important factors:
1. Politicians' websites are terrible because they're generally clueless about technology. Contrary to popular belief at the time, the Internet wasn't just a series of tubes and data wasn't moved around in great big dump trucks.
2. They're terribly slow to make decisions. Think of all the hemming and hawing to get anything done in Washington and now imagine that it's their own money on the line.
3. They try to cut deals instead of paying you. In fact, you should be paying them to do their website. Think of all the great exposure you're going to get!
4. They are, by the very nature of getting into that world, mostly shady and narcissistic.
That last point can't be stressed enough. Our political clients were a nightmare. Maybe it was that we were working in Miami, which isn't exactly known for its ethical politicians; but it didn't seem to matter where the race was taking place. Once we had a well known political upstart steal an idea we pitched him on and use it to break single-day fundraising records, we decided this market wasn't worth the trouble.
So we moved away from politicians, and onto another seemingly underserved market: Athletes. I won't bore you with too many details - but suffice it to say that the problems we experienced with athletes were very similar to the politicians. Cheap, technologically illiterate, shady. 
It became clear that we needed to work on a wider range of projects, so we decided to work on designing and developing sites for a variety of small businesses. However, we had a big problem. We spent so much time trying to close deals with politicians and athletes, that we had an extremely limited portfolio. No one wanted to be one of the first test cases for our new company. 
This led to us making the horrible decision to take a hit on our early projects in order to build up our client list. At first we did a few small projects for free, just to get something in our portfolio. Then, for too long, we took projects for dirt cheap. We didn't give ourselves nearly enough credit for the value of the work we had already done; especially considering three of the five original founders worked with high end brands at their previous agency.
In the first year, we made $16,000. For 5 people. It was fucking nuts. 
We had to get creative with ways to save money. Luckily, Luke was really good at getting hookups, and was even able to make money hosting a weekly BBQ at The Standard in Miami Beach with his roommate (free burgers and drinks!). 
Even luckier, Alex and I were able to move from South Beach into a rent free house owned by his family in Little Havana, the old, predominantly Cuban area of Miami. We were the youngest people in the neighborhood by a solid 50 years, and our place needed quite a bit of TLC; but before too long it felt like home.
Nobody gets it.
Your social life is one of the biggest sacrifices you have to make if you're serious about going the startup route; especially if you decide to bootstrap, like us. 
We consistently had to cancel nights out with friends. We worked all the time, and didn't have the money to do anything, anyway. It was hard for a number of reasons, but the most difficult thing for us to grasp was that our friends and family just didn't get it. And neither will yours. Trust me. No matter how great your friends and family are, unless they've started their own company, they won't understand what you're going through. It's not that they don't care, they really do. It's just that they can't. 
When you get a steady paycheck every few weeks from an employer, it's really difficult to wrap your head around the idea that in a startup your next paycheck is never guaranteed. And that sometimes - often for a long time -  you don't get paid at all.
Another thing we didn't realize is just how ego-shattering this lifestyle could be. There were times that I wondered what the hell I was doing. I didn't go to graduate school to make less than I made in high school as a lifeguard. Being broke mid to late twenties is very different than in your early twenties. It's not the same as being flat broke in college, when it didn't matter because everyone else was too, and you only needed enough money for Natty Light. 
It's hard to watch as your friends and peers excel in their careers, enjoy stability in their lives, and seem to have it all together. As much as you want to be happy for them, you can't. You just see them living on easy street while your emotions are on a perpetual roller coaster.
Then things got better, then worse, then better, then...
Things began to pick up for us after the first year, and by year three we were down one founder, but were making a decent amount of money. We were even able to get a pretty sweet office on South Beach in a dog-friendly building. But the client world, even moreso than life in general, is fickle. One day you're enjoying the freedom of running your own business; the next you realize that working for clients isn't all that different from working for a boss. In fact, it can be much, much worse .
As the price tags grew, and the projects became more complex, so did the demands for control from our clients. We ended up pouring our heart and souls into projects that were ultimately not ours, and we had to sacrifice our vision at every step of the way. It became apparent that something had to change. Now we just had to figure out what we were going to do.
Next up: Life would be so much easier without clients. Right?